Airlines with flights from Chicago to Cancun

There are two airlines with scheduled flights between MDW and CUN. Southwest is the only airline with non-stop flights from Midway International Airport to Cancun International Airport and the flight time is 3 hours and 40 minutes.

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Choose airline

Schedules

Non-stop with Southwest Airlines

  • Total flight time: 3 hours and 40 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 14 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
MDW
Direct
CUN
 
Flight
Mon
Jun 10
Tue
Jun 11
Wed
Jun 12
Thu
Jun 13
Fri
Jun 14
Sat
Jun 15
Sun
Jun 16
WN218
09:40
09:40
09:40
09:40
09:40
06:15
09:05
WN216
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----
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----
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12:55
13:00
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - CUN

The timetable & schedule information was updated at 2024-03-15

Via Houston with Southwest Airlines

  • Total flight time: 5h 30m - 11h 50m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 28 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
MDW
 
Via HOU
 
CUN
 
Flight
Mon
Jun 10
Tue
Jun 11
Wed
Jun 12
Thu
Jun 13
Fri
Jun 14
Sat
Jun 15
Sun
Jun 16
WN3928
WN318
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05:00
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WN4767
WN307
05:50
06:20
06:20
05:50
05:50
05:55
05:10
WN4767
WN305
05:50
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05:50
05:50
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05:10
WN1563
WN1609
07:30
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07:30
07:30
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05:15
WN5113
WN1609
05:15
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05:15
05:15
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WN2638
WN386
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05:20
05:25
WN3341
WN318
05:20
05:25
05:25
05:20
05:20
06:20
05:20
WN2374
WN1607
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05:25
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WN4533
WN728
05:25
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05:25
05:25
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WN4989
WN1134
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05:30
WN4533
WN708
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05:35
05:35
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06:25
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WN508
WN1609
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05:45
05:45
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WN1122
WN1134
06:15
05:50
05:50
06:15
06:15
05:55
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WN868
WN1985
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05:50
WN868
WN1995
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----
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----
05:50
----
WN1906
WN307
06:05
----
----
06:05
06:05
----
----
WN1906
WN751
06:05
----
----
06:05
06:05
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WN4745
WN751
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06:15
06:15
----
----
----
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WN1180
WN1985
07:05
----
----
07:05
07:05
----
----
WN1180
WN1995
07:05
----
----
07:05
07:05
----
----
WN3702
WN1995
----
07:15
07:15
----
----
----
----
WN2015
WN1609
----
----
----
----
----
----
07:20
WN2252
WN307
07:20
08:00
08:00
07:20
07:20
----
----
WN4220
WN318
07:25
07:55
07:55
07:25
07:25
----
07:35
WN3393
WN728
07:35
----
----
07:35
07:35
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WN704
WN751
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08:00
08:00
----
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WN106
WN386
08:00
----
----
08:00
08:00
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WN1865
WN1134
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----
----
----
----
08:00
----
WN4259
WN386
----
08:05
08:05
----
----
----
----
WN2252
WN317
----
----
----
----
----
----
08:10
WN1731
WN728
----
08:35
08:35
----
----
----
08:10
WN105
WN317
----
----
----
----
----
08:15
----
WN1718
WN317
----
----
----
----
----
08:15
----
WN1627
WN1995
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----
----
----
----
----
08:25
WN1954
WN1613
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----
----
----
----
08:35
----
WN5092
WN1995
08:40
----
----
08:40
08:40
----
----
WN3325
WN318
08:50
----
----
08:50
08:50
----
----
WN1467
WN1995
----
08:55
08:55
----
----
----
11:00
WN208
WN325
----
09:10
09:10
----
----
----
----
WN3252
WN317
----
----
----
----
----
10:35
----
WN3450
WN325
10:35
----
----
10:35
10:35
----
----
WN714
WN325
10:40
----
----
10:40
10:40
----
----
WN3834
WN386
----
11:00
11:00
----
----
----
----
WN3473
WN325
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----
----
----
----
----
11:05
WN2518
WN325
11:40
----
----
11:40
11:40
----
----
WN4883
WN325
12:10
----
----
12:10
12:10
----
----
WN647
WN325
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----
----
----
----
----
13:05
WN1557
WN325
----
13:10
13:10
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - CUN

The timetable & schedule information was updated at 2024-03-15

Via Baltimore with Southwest Airlines

  • Total flight time: 6h 10m - 10h 30m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 18 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
MDW
 
Via BWI
 
CUN
 
Flight
Mon
Jun 10
Tue
Jun 11
Wed
Jun 12
Thu
Jun 13
Fri
Jun 14
Sat
Jun 15
Sun
Jun 16
WN3928
WN318
----
----
----
----
----
05:00
----
WN4767
WN307
05:50
06:20
06:20
05:50
05:50
05:55
05:10
WN4767
WN305
05:50
----
----
05:50
05:50
----
05:10
WN1563
WN1609
07:30
----
----
07:30
07:30
----
05:15
WN5113
WN1609
05:15
----
----
05:15
05:15
----
----
WN2638
WN386
----
----
----
----
----
05:20
05:25
WN3341
WN318
05:20
05:25
05:25
05:20
05:20
06:20
05:20
WN2374
WN1607
----
----
----
----
----
05:25
----
WN4533
WN728
05:25
----
----
05:25
05:25
----
----
WN4989
WN1134
----
----
----
----
----
----
05:30
WN4533
WN708
----
05:35
05:35
----
----
06:25
----
WN508
WN1609
----
05:45
05:45
----
----
----
----
WN1122
WN1134
06:15
05:50
05:50
06:15
06:15
05:55
----
WN868
WN1985
----
----
----
----
----
----
05:50
WN868
WN1995
----
----
----
----
----
05:50
----
WN1906
WN307
06:05
----
----
06:05
06:05
----
----
WN1906
WN751
06:05
----
----
06:05
06:05
----
----
WN4745
WN751
----
06:15
06:15
----
----
----
----
WN1180
WN1985
07:05
----
----
07:05
07:05
----
----
WN1180
WN1995
07:05
----
----
07:05
07:05
----
----
WN3702
WN1995
----
07:15
07:15
----
----
----
----
WN2015
WN1609
----
----
----
----
----
----
07:20
WN2252
WN307
07:20
08:00
08:00
07:20
07:20
----
----
WN4220
WN318
07:25
07:55
07:55
07:25
07:25
----
07:35
WN3393
WN728
07:35
----
----
07:35
07:35
----
----
WN704
WN751
----
08:00
08:00
----
----
----
----
WN106
WN386
08:00
----
----
08:00
08:00
----
----
WN1865
WN1134
----
----
----
----
----
08:00
----
WN4259
WN386
----
08:05
08:05
----
----
----
----
WN2252
WN317
----
----
----
----
----
----
08:10
WN1731
WN728
----
08:35
08:35
----
----
----
08:10
WN105
WN317
----
----
----
----
----
08:15
----
WN1718
WN317
----
----
----
----
----
08:15
----
WN1627
WN1995
----
----
----
----
----
----
08:25
WN1954
WN1613
----
----
----
----
----
08:35
----
WN5092
WN1995
08:40
----
----
08:40
08:40
----
----
WN3325
WN318
08:50
----
----
08:50
08:50
----
----
WN1467
WN1995
----
08:55
08:55
----
----
----
11:00
WN208
WN325
----
09:10
09:10
----
----
----
----
WN3252
WN317
----
----
----
----
----
10:35
----
WN3450
WN325
10:35
----
----
10:35
10:35
----
----
WN714
WN325
10:40
----
----
10:40
10:40
----
----
WN3834
WN386
----
11:00
11:00
----
----
----
----
WN3473
WN325
----
----
----
----
----
----
11:05
WN2518
WN325
11:40
----
----
11:40
11:40
----
----
WN4883
WN325
12:10
----
----
12:10
12:10
----
----
WN647
WN325
----
----
----
----
----
----
13:05
WN1557
WN325
----
13:10
13:10
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - CUN

The timetable & schedule information was updated at 2024-03-15

Via Atlanta with Delta Air Lines

  • Total flight time: 5h 07m - 9h 22m.
  • Sky Team Alliance
  • 14 flights per week
MDW
 
Via ATL
 
CUN
 
Flight
Mon
Jun 10
Tue
Jun 11
Wed
Jun 12
Thu
Jun 13
Fri
Jun 14
Sat
Jun 15
Sun
Jun 16
DL1285
DL598
06:00
06:00
06:00
06:00
06:00
06:00
06:00
DL1285
DL592
06:00
06:00
06:00
06:00
06:00
06:00
06:00
DL1285
DL586
06:00
06:00
06:00
06:00
06:00
06:00
06:00
DL1063
DL1939
10:41
10:41
10:41
10:41
10:41
10:41
10:41
DL2417
DL1939
12:45
12:45
12:45
12:45
12:45
12:45
12:45
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - CUN

The timetable & schedule information was updated at 2024-03-15

Via Saint Louis with Southwest Airlines

  • Total flight time: 5h 00m - 9h 10m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 10 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 (winglets) Passenger/BBJ1
MDW
 
Via STL
 
CUN
 
Flight
Mon
Jun 10
Tue
Jun 11
Wed
Jun 12
Thu
Jun 13
Fri
Jun 14
Sat
Jun 15
Sun
Jun 16
WN3928
WN318
----
----
----
----
----
05:00
----
WN4767
WN307
05:50
06:20
06:20
05:50
05:50
05:55
05:10
WN4767
WN305
05:50
----
----
05:50
05:50
----
05:10
WN1563
WN1609
07:30
----
----
07:30
07:30
----
05:15
WN5113
WN1609
05:15
----
----
05:15
05:15
----
----
WN2638
WN386
----
----
----
----
----
05:20
05:25
WN3341
WN318
05:20
05:25
05:25
05:20
05:20
06:20
05:20
WN2374
WN1607
----
----
----
----
----
05:25
----
WN4533
WN728
05:25
----
----
05:25
05:25
----
----
WN4989
WN1134
----
----
----
----
----
----
05:30
WN4533
WN708
----
05:35
05:35
----
----
06:25
----
WN508
WN1609
----
05:45
05:45
----
----
----
----
WN1122
WN1134
06:15
05:50
05:50
06:15
06:15
05:55
----
WN868
WN1985
----
----
----
----
----
----
05:50
WN868
WN1995
----
----
----
----
----
05:50
----
WN1906
WN307
06:05
----
----
06:05
06:05
----
----
WN1906
WN751
06:05
----
----
06:05
06:05
----
----
WN4745
WN751
----
06:15
06:15
----
----
----
----
WN1180
WN1985
07:05
----
----
07:05
07:05
----
----
WN1180
WN1995
07:05
----
----
07:05
07:05
----
----
WN3702
WN1995
----
07:15
07:15
----
----
----
----
WN2015
WN1609
----
----
----
----
----
----
07:20
WN2252
WN307
07:20
08:00
08:00
07:20
07:20
----
----
WN4220
WN318
07:25
07:55
07:55
07:25
07:25
----
07:35
WN3393
WN728
07:35
----
----
07:35
07:35
----
----
WN704
WN751
----
08:00
08:00
----
----
----
----
WN106
WN386
08:00
----
----
08:00
08:00
----
----
WN1865
WN1134
----
----
----
----
----
08:00
----
WN4259
WN386
----
08:05
08:05
----
----
----
----
WN2252
WN317
----
----
----
----
----
----
08:10
WN1731
WN728
----
08:35
08:35
----
----
----
08:10
WN105
WN317
----
----
----
----
----
08:15
----
WN1718
WN317
----
----
----
----
----
08:15
----
WN1627
WN1995
----
----
----
----
----
----
08:25
WN1954
WN1613
----
----
----
----
----
08:35
----
WN5092
WN1995
08:40
----
----
08:40
08:40
----
----
WN3325
WN318
08:50
----
----
08:50
08:50
----
----
WN1467
WN1995
----
08:55
08:55
----
----
----
11:00
WN208
WN325
----
09:10
09:10
----
----
----
----
WN3252
WN317
----
----
----
----
----
10:35
----
WN3450
WN325
10:35
----
----
10:35
10:35
----
----
WN714
WN325
10:40
----
----
10:40
10:40
----
----
WN3834
WN386
----
11:00
11:00
----
----
----
----
WN3473
WN325
----
----
----
----
----
----
11:05
WN2518
WN325
11:40
----
----
11:40
11:40
----
----
WN4883
WN325
12:10
----
----
12:10
12:10
----
----
WN647
WN325
----
----
----
----
----
----
13:05
WN1557
WN325
----
13:10
13:10
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - CUN

The timetable & schedule information was updated at 2024-03-15

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